3-氰基-2-(三甲基甲硅烷基)苯基硼酸 | 1057732-45-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 3-氰基-2-(三甲基甲硅烷基)苯基硼酸
• 英文名称: 3-cyano-2-(trimethylsilyl)phenylboronic acid
• 英文别名: (3-Cyano-2-trimethylsilylphenyl)boronic acid
• CAS: 1057732-45-2
• 化学式: C₁₀H₁₄BNO₂Si
• 分子量: 219.123
• InChiKey: RGINEXXBTZFDLI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.22
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  64.2
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-氰基-2-(三甲基甲硅烷基)苯基硼酸 在 一氯化碘 作用下， 以 氯仿 为溶剂， 反应 6.0h， 以79%的产率得到3-cyano-2-iodophenylboronic acid
  参考文献：
  名称：

  Electrophilic ipso-iodination of silylated arylboronic acids

  摘要：

  Silylated functionalized arylboronic acids were converted into corresponding iodinated arylboronic acids in good yields via the electrophilic ipso-desilylation effected with iodine chloride in refluxing CHCl3. Disilylated arylboronic acids were susceptible to diiodination. In addition, the structural characterization and reactivity of a novel sterically hindered ortho-silylated diarylborinic ester were reported. The potential of selected iodinated phenylboronic acids as monomers for the SuzukieMiyaura cross-coupling polymerization was demonstrated. (C) 2010 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2010.08.016
• 作为产物：
  描述：

  3-bromo-2-(trimethylsilyl)benzonitrile 在 正丁基锂 、 硼酸三甲酯 、 硫酸 作用下， 以 四氢呋喃 为溶剂， 反应 0.25h， 以82%的产率得到3-氰基-2-(三甲基甲硅烷基)苯基硼酸
  参考文献：
  名称：

  Selective Generation of Lithiated Benzonitriles: the Importance of Reaction Conditions

  摘要：

  Lithiated benzonitriles can be generated in high yields from reactions of bromobenzonitriles with n-BuLi in THF under standard cryogenic conditions (ca. -70 degrees C) provided the reverse addition mode is employed. The resultant aryllithiums are fairly stable at temperatures up to -60 degrees C. The formation of lithiated benzonitriles via Br/Li exchange under normal addition mode conditions is plagued by deprotonation and extensive CN-addition reactions. The generation of related aryllithiums from disilylated bromobenzonitriles is comparatively less sensitive to reaction conditions.

  DOI：

  10.1021/jo8013808